Gary Henderson defeated Andrew Richardson 7-6 7-6 in the Great Britain 3 Masters 1 semi-final on grass. The upset overturned the form book — Andrew Richardson came in leading the head-to-head 2–0, but Gary Henderson had been the form player, winning 3 of their last 6 on grass. Gary Henderson claimed a first win over Andrew Richardson in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1995-04-24 | Great Britain 2 Masters 3 | R16 | clay | Andrew Richardson | 6-2 6-3 |
| 1993-11-27 | Pakistan Masters 4 | R32 | hard | Andrew Richardson | 6-3 6-7 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.